Ethyl trifluoroacetate → 4,4,4-Trifluoro-1-(pyridin-2-yl)butane-1,3-dione

HRID 11878

Reaction equation

HRID 11878 reaction equation
C(O[C:4](=[O:9])[C:5]([F:8])([F:7])[F:6])C.[N:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16](=[O:18])[CH3:17].C[O-].[Na+]>CO>[F:8][C:5]([F:6])([F:7])[C:4](=[O:9])[CH2:17][C:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][N:10]=1)=[O:18]

Participants

5

Reactant 3

HCID 9794Ethyl trifluoroacetateHCID 142862-AcetylpyridineHCID 10942334Sodium Methoxide

Product 1

HCID 27714784,4,4-Trifluoro-1-(pyridin-2-yl)butane-1,3-dioneYield 81.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Trifluoro-acetic acid ethyl ester (9.82 mL, 82.5 mmol) was added to a solution of 1-pyridin-2-yl-ethanone (5.00 g, 41.2 mmol) in methanol (40 mL) containing sodium methoxide (61.8 mmol). The reaction mixture was heated at reflux overnight, concentrated under reduced pressure and acidified with aqueous hydrochloric acid (10%). The aqueous solution was extracted with ethyl acetate (10×50 mL). The organic layers were collected, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel to give 4,4,4-trifluoro-1-pyridin-2-yl-butane-1,3-dione (7.26 g, 81%).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. extractionThe aqueous solution was extracted with ethyl acetate (10×50 mL)
  5. customThe organic layers were collected
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude product was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-041f2cc851b84257b82bcd81cc91efb6
Source dataset
uspto-grants-2006_08
Patent number
US07098335B2

Linked notes

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